How I Quit My Day Job


joyfear“Twenty years from now you will be more disappointed by the things that you didn’t do than by the ones you did do. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover.” – Mark Twain

Well, I did it.  I gave notice to my employer.  60 more days, and I am leaving my job.

This is not going to be a “I left my cubicle job, finally” post.  You have probably read enough of those.  This is different.

I have been fortunate in my life that I have pursued work I am passionate about.  It has always been in the field of music and education, and I am lucky to have had the opportunity to continue with it while many around me have not.

I have gone from to performer, to teacher, to administrator, all the while moving up the salary scale.  At one point, I began making a salary that I never dreamed I would make.  After all, I used to make $18,000 a year after college and I was totally happy!

A little over a year ago, I surveyed my situation and realized that lifestyle inflation had hit me hard.  I justified it by saying to myself that I was in a field I loved, not trapped in a cubicle, so it was okay to have debt.  After all, I would work forever, I told myself.

Nevertheless, I had had enough.  I went on a mission to viciously pay off debt and get rid of the “stuff” in my life.  One year later, I began having new thoughts pop up:

“Am I doing work I love 100% of the time?”

“Even though I like my work a lot, am I trapped in it because of my debt?”

“Am I settling?”

“Can I stick with this job for 10+ more years?”

After one year of massive debt payoff, I decided that I would try and stick with my job but attempt extreme early retirement.  After doing the math, I figured that I could pay off all of my debt plus my mortgage and retire at the age of 46 (I’m 39 now).

After a year-and-a-half, I changed my my mind.  I asked myself, “why I would choose to “sweat out” a job I even remotely disliked for future retirement”?  That is not, and has never been, the way I operate.  I decided to split the difference and prepare to take a 6-12 month “mini-retirement” instead.

It was a pretty cool challenge; I needed to “beef up” my side income pursuits while at the same time scaling down expenses.  After all was said and done, it was still going to be scary…I was ditching a 6-figure income, plus pension and benefits.

Here’s what I did to prepare for the “mini-retirement”:

1.  I got out of debt and saved an emergency fund. These two financial moves were enormous for me. I wasn’t going to quit my day job without getting out of debt first, and without an adequate emergency fund. None of this would have been possible without this move. I have a family to worry about. I have almost eliminated my debt and saved a decent emergency fund, though it’s not as large as I’d like.

2.  Increased my side hustle income.  My “side hustles” are teaching trombone at a couple of universities and privately…hardly a “hustle”, since I adore the work and wish it could be full time.  I have worked to recruit new students, and I’ve also taken my new-found skills as an administrator to promote myself as an asset to institutions as a teacher trainer, or whatever!

3. Find health insurance.  This one was huge!  It is also a necessity since I have a wife and two kids.  I found an organization that could use me as a consultant (music education) and I asked to be paid just in health benefits.  They said yes!  Again, I drew upon skills I have learned over the years and found an organization in need of those skills.  Ask yourself: what type of skills do you have that are marketable?  Are they honed?  If so, great!  If not, sharpen the saw a bit by taking a few more classes, either online or at a local school.  The payoff is huge.

4.  Pare down my expenses to the bones.  I have discussed this in many posts.  By creating a budget, I was able to monitor and track expenses carefully with my wife.  Two years later, we have hundreds less per month in expenses!

5.  Get rid of stuff.  We got rid of so much crap we didn’t need, and we continue to ditch our stuff.  It’s not necessary, and when I figured that less stuff = more freedom, it was easy to get rid of it all.  If “stuff” is holding you back from finding work you love…ditch it!

What Happens Next?

My last day is the end of June, and then I go off to run my camp.  After that…who knows?

Not that much will change with this blog at least. I plan to continue to focus on putting out the best content I can.

I will be leaving myself open for job opportunities that align only with my passions.  I can afford to do this for one year, for sure.

Financially, if nothing changes, I will be just fine. If anything changes, I anticipate it changing for the better…and if so, I will have an even better year than I imagined!  But if it changes for the worse, I will always be able to find another day job.

It’s going to be scary and fun being self-employed…failure and success are dependent completely on me.

It all comes back to the debt and the “stuff”.  By getting rid of this mountain of unnecessary garbage, I have opened up “space” in my life for other (non-material) things:  Time with my kids, work I enjoy, or just free time to enjoy living.  Scary, at times, yes … but extremely liberating!


  1. Great post bro! Love the attitude and the guts you have. I too quit my “day job” four years and have never looked back…enjoy this new adventure, Tony!

    • Thanks, Phil! I know you chose to live your life as an adventure as well (perhaps a guest post is in your future??). Thanks for dropping by, my friend.

  2. Congratulations, Tony! Exciting!
    You’re going to do great things and never look back.

  3. Congrats Tony, but you’d have a lot more time in your life if you wouldn’t talk to lame brain soft-skulled parents for 45 minutes at the beginning of every day! And yes, I’m talking about me.

  4. Awesome Tony, congratulations! if you can make basic expenses with trombone lessons and just dip into savings for treats, I am betting this mini retirement will last much longer.
    Pauline recently posted…Friday recap, a booked flight and header iconsMy Profile

  5. Congrats, Tony! I hope you find what you’re looking for.

  6. This is jump out of my seat exciting, Tony! This is my favorite post on your site, and you have had some great ones! You not only laid it on the table for us all to see, you carefully and methodically walked us through it. Brilliantly written. Thank you!

    What creative ways to procure benefits, income, and – the best part of all? You are doing it because you asked yourself the tough questions and decided to fully pursue your passions. I can only imagine the impact this will have on your future – and that of your family. Super wow! Enjoy these next few weeks! What fun!
    Tammy R recently posted…Mindfully Picking Up the SlackMy Profile

    • Thanks for this, Tammy. I am flattered that you are a reader! Basically, I had the latitude to craft an interesting “alternate” career by downsizing enough to allow it to happen. With the inflated lifestyle of 3 years ago, there was no option to even think about this. The question is, “what is enough..and then some?”

  7. Tony!!! This is fabulous to see someone unwilling to settle despite them already having pretty damn good. And you had the wisdom not to wait until you were 60. Well played, my man. Well played. I am extremely intrigued by this consulting job of yours related to mus ed that also pays you with health benefits.

    Side hustles are my main concern right now. I suppose my whole life is a combination of them, but I am always looking for better ones that give a bit more bang for the buck or that are more fulfilling or both. Why the hell not, right?

    Can’t wait to read your future posts on your experience with the whole affair. If it went anything like our transformation, you’ll freakin’ love it!!!!!
    cj recently posted…Mindfully Picking Up the SlackMy Profile

    • Thanks, CJ. I must admit: after many years of struggle, I have had it “pretty darn good” for the past few years. It was from hard work, though, and putting myself in the position to be lucky. But the purchasing of expensive stuff definitely skewed my view of work and career, and I am glad to have righted the ship.

      As far as consulting, I am good at a few things…and one of them is building music programs. Organizations need help doing this, and I have slowly put myself in the position to help them! I thought I would ask for benefits in lieu of salary, and it worked :).

      The increase of side hustles as it relates to work has been a long term project…if I could graph it, it would look like a sloooooooowly rising diagonal line!

      Thanks for reading, as always!

  8. Congrats! Very exciting. Hope to do this someday soon.
    Michelle recently posted…Relationships and Money: Talk is Not CheapMy Profile

  9. Congratulations Tony. I have to admit, when I read the title to this post, I assumed it would be a guest post! How exciting!
    My last 25 years have been side hustling and I wouldn’t have it any other way. I’ve been busier this past year than any other and all from non-traditional jobs. I love it! Can’t wait to hear your journey as it unfolds. I’m always inspired by your posts.

    • Hey Keve, As musicians we have had to hustle quite a bit, haven’t we? It is a fun type of hustle, but it is a hell of a lot of work. Paying off debt, downsizing, and getting rid of stuff has now allowed me to do this with a different set of eyes. Let’s see what happens!

  10. Nice work Tony. Glad you were able to do this and I am sure you will have a blast for this next year. You have worked hard to make it happen and that is really the biggest accomplishment here.
    Grayson @ Debt Roundup recently posted…Feeling Good Friday: Reaching Out to HelpMy Profile

    • Grayson, I appreciate You following my story for this long. I am very interested to see what the next year will bring, and I will have a lot of fun writing about it!

  11. Congrats Tony!

    My guess is that once you leave your job, you’ll put more into your online business which will result into more income..

    ~ darlene :)
    Darlene recently posted…How To Outsource Cheaply & EffectivelyMy Profile

  12. Tony! This is incredibly exciting and I’m so excited for you as you move into the next phase of your life. The quote by Mark Twain is one my favorites too! My biggest concern for you would have been giving up your medical benefits but I love your creative thinking in finding a way to get someone else to cover you and your family. Very, very smart! I look forward to hearing how the journey goes for you and what you learn about yourself. Good luck and congratulation on taking this big step!
    Shannon @ The Heavy Purse recently posted…Blog Round-Up: Supersized EditionMy Profile

  13. Well done Tony! I wish you all the success along your new path in life. Cheers!
    Canadian Budget Binder recently posted…PF Weekly Reading List #17-Customer Service, Business Suicide And Social MediaMy Profile

  14. Congrats Tony! It’s been great to read your words of wisdom and see how your life has blossomed. I’m truly happy for you and your family. Keep it up!

    • Thanks, Susan. That means an awful lot to me. It has been an interesting life so far, hasn’t it?? Never a dull moment, indeed.

  15. Uhhh… Wow.

    You are officially added to my private badass list.

    Well done, my friend.
    Patrick recently posted…Celebrating the tragic death of a commuteMy Profile

    • Patrick, thanks man. Been very cool to have you as a visitor and read your work as well. The Twain quote is a favorite…especially since we only do this life thing once…

  16. Adrienne says:

    Congratulations Tony! What a beautiful way to live — clear-eyed and open hearted, good things will come but I don’t think that’s the point. THIS is great.

  17. Congrats!! Just found this through a tweet PT money sent out. Great idea on the health insurance.
    Makinsensebabe Babe recently posted…Email Script: Oh Hey Financial Advisor, Why You Sucker Punching Me With So Many Funds??My Profile

    • Thanks for visiting! Like I noted earlier in comments, it is a shame that insurance is such a detractor for finding a better job. That said, it pays to be innovative and this time it worked out!

  18. Moving from employed to self-employed. That’s a big jump. But it’s a risk worth taking.

    You’re doing what a lot of other people wish they could do. That’s pretty cool.
    Steve recently posted…9 Ways to Be UnremarkableMy Profile

  19. Well done on deciding to have a go and I do admire your courage. As to me – the date is set for five years from now but watch this space. Ironically, I am enjoying my job much more since I decided this (suddenly accountants lost their hold and power); as to my job I’ve always loved it. So no retirement for me – but I don’t want to be part of any organisation and have to ask for permission to go to the bathroom (slight exaggeration) ever again. Or be told that students need loads of guidance (thus stifling their creativity) or that they are the customer (I see them as my psrtners in learning).

    Well done again, and keep us posted on how it is going.
    maria@moneyprinciple recently posted…Shopping for SatisfactionMy Profile

    • Very cool how you are enjoying the work now that you know it is finite. I felt the same way, for sure Maria. Will absolutely document the journey!

  20. I am a big follower of the Vedas and yog. One of the components of taking control over your mind and self, as propounded in the Vedas, is ‘aparigraha’ — non-hoarding of unnecessary things or ‘stuff’, like you aptly call it :). Mahatma Gandhi was known to practice it. I know it is easier said than done, but it is a great, great quality. I admire you for stepping into this courageous and purposeful terrain. In the true sense of the word, it includes not just material things, but thoughts as well.

  21. Tony, I am so very happy for you!!! This is what debt payoff is all about – being able to choose what we do and do what we love. Congrats, friend! You did it!
    Laurie @thefrugalfarmer recently posted…Some Link Love, and The Frugal Farmer’s First Staff ContributorMy Profile

  22. Yay, Tony. That’s fantastic. I can feel your enthusiasm for the next phase of life. You’ve had some huge accomplishments this year. I think for myself and why I decided to change the way I was living was one of your questions, “Can I do this for 10+ years?” which made me cringe, literally. I’ve found by getting rid of so much debt, and cutting back my work schedule, I don’t mind it, and I can do what I’m doing now for as long as it feels right. With taking control of your money and letting it work for you, you have so many more options than when you work for it. Congratulations.
    Kim@Eyesonthedollar recently posted…Eyes on the Dollar 20/20 Roundup #35- Goodbye to an Old FriendMy Profile

    • Sorry to make you cringe there, Kim! Cutting back your schedule must have felt pretty good. IT really all comes down to lowering our personal overhead (debt) so we can make sound, informed decisions on our life…right?

  23. Awesome! I admire your decision to leave the harbour and follow your passions, I can only hope you end up at another port that aligns with your vision! I hope you’ve got your goals and such down to a pin head, I can guarantee it’ll help on the journey..

    Have an absolutely awesome time doing it all, Tony!
    Nick Goodall recently posted…How To Eat HealthyMy Profile

  24. I love hearing stories like this! Great job. I think it super cool how you bargained for health insurance – that’s something I will keep in mind for the future.
    CF recently posted…Updates: April 21 – 27My Profile

  25. Wow, that’s a big,bold move. Congrats! I don’t know that I’d quit my job even if I were miserable in it, but I just started my career so that might change in the future.
    Daisy @ Prairie Eco Thrifter recently posted…Friday Links – Back In The Country EditionMy Profile

  26. Amazing and inspiring. A lot of people should follow your example. I like your bargain with your music insurance and I also love the idea that you are keeping track of everything.
    KC @ genxfinance recently posted…How to Save Money on Food With These 5 TipsMy Profile

  27. You’re gonna be livin’ the dream Tony. I’m jealous. But good for you. That’s the ultimate goal right? To be your own man. To live a self-determined life. Sounds like you’ve worked your ass off to get there. So you earned it. Congrats man.

    I hope you’ll be dedicating a chunk of your extra time to this blog. You can take it pretty damn far you know.

    Trevor recently posted…New Theme: Whatcha Think? And What’s With the Damn Bounce Rate?My Profile

  28. Exciting Story.. And I’m sure you must be in your own freedom.

    Hope i will do it soon!!
    Josh recently posted…Download PDFBinder to Merge Multiple PDF DocumentsMy Profile

  29. You are very lucky since you know what you want and acted on making your goals possible; now you’re on a new road to freedom. Not many people can get rid of debt totally like you did. The key is to dream, then pursue it. Good luck and enjoy your clutter-free life.
    Amy Turner recently posted…If You Had All the Money in the World, What Would You Buy Your Mom?My Profile

  30. Congrats Tony! You’ve reached the state that I’m striving for!
    Jose recently posted…My Six Thousand Dollar Boat RideMy Profile

  31. Fantastic Tony!

    I am starting my fourth month working for myself, and I am so happy that I made the decision. I used to enjoy my job as well as an environmental investigator, and from time to time I think about it. But this freedom, flexibility, and ability to take action on all of my ideas is one of the biggest highs of my life. I have already completed several projects that I would never have had the time to do (or not for a year or two) had I stayed at my job.

    Actually, in three months, I have yet to question any decision I have made. That’s a good sign, though I know things may change down the road.

    Anyway, congratulations, and enjoy these last months at your job as well! After all, life is now.
    Amanda L Grossman recently posted…The Amish Next Door: How they Manage their Children’s MoneyMy Profile

    • Thanks Amanda! I know that you are in the thick of it, and I commend you for all of your hard work! We shall compare stories along the way!

  32. Great Post! Having no job at all is not the end. Employment is one of the ways to earn money. However, there is always a limit in employment. If you want more, engage in business and investment because it can give more and money will work for us.

  33. Still getting caught up on my blog reading and missed this. HUGE CONGRATS!! can’t wait to see what’s in store for you!
    Catherine recently posted…Don’t Finance a TV, Win One Here Instead!My Profile

  34. Great to see that you finally took the big leap Tony. Most of us wouldn’t have the courage to leave our primary jobs. Getting out of debt and building an emergency fund were great decisions – now you can live the way you like without having to worry about paying off those darn loans. Good luck ahead!
    Harry @ Smart Money Junction recently posted…15+ Ways to Create Multiple Streams of IncomeMy Profile

  35. It’s truly amazing, the thoughts that go on in our heads in the 21st century. I cannot fathom anyone a generation or two before us would think about “quitting a day job” and for that matter anyone knowing that it would be possible. Working a job has been for many generations a matter of survival. It has been the only thing that has put food on the table and provided what has been needed for other necessities in life.

    I do not mean to put down this post, but the more I see ideas like this, I just have to imagine where it all started. Who was it that started this revolution of quitting a day job or doing work you enjoy? I’d like to think workers of the 20th century thought to themselves, “I wish I could do work I loved” but I am more inclined to think they would not have known any better, especially the farther we go back, like to the 19th century.
    Scott @ Youthful Investor recently posted…5 Great Books to Learn Asset AllocationMy Profile

    • No offense taken! Let me put it this way: I still teach many music students whose parents won’t let them go into the field; they want them to be the doctors and lawyers. Millions of people have not followed their dreams because of reasons like this…


  1. […] For me, it helps to read success stories like Tony’s post over at We Only Do This Once on how he quit his day job.  Tony and his family worked hard for almost two years, sacrificing LOTS so that they could pay […]

  2. […] How I Quit My Day Job is a good post from Tony at We Only Do This Once. Anyone interested in financial independence and pursuing a lifestyle of doing what they “want” to do and not what they “have” to do should read this. Tony explains how he did it and the steps he took to get there. This lines up with my goals quite nicely. I read this a few times just to make sure I didn’t miss anything! […]

  3. […] How I Quit My Day Job at We Only Do This Once. Yay Tony! What a difference a year can make. […]

  4. […] @ We Only Do This Once writes How I Quit My Day Job – Well, I did it. I gave notice to my employer. 60 more days, and I am leaving my job. […]

  5. […] @ We Only Do This Once writes How I Quit My Day Job – Well, I did it. I gave notice to my employer. 60 more days, and I am leaving my job. […]

  6. […] @ We Only Do This Once writes How I Quit My Day Job – Well, I did it. I gave notice to my employer. 60 more days, and I am leaving my job. […]

  7. […] am thrilled for Tony that he is quitting his day job and will take a “mini […]

  8. […] @ We Only Do This Once writes How I Quit My Day Job – Well, I did it. I gave notice to my employer. 60 more days, and I am leaving my job. […]

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